2,4,6-Trimethylaniline → HCID 66795765, compound

Participants

Reaction Steps

A mixture of 4.80 g (15.0 mmol) of 6-{2-[(tert-butylamino)methyl]-1-naphthyl}pyridine-2-carbaldehyde and 2.00 g (15.0 mmol) of 2,4,6-trimethylaniline in 50 ml of dry ethanol was refluxed overnight. The resulting mixture was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane-methanol-triethylamine=100:10:1, vol.). Yield 5.80 g (88%) of orange oil. Anal. calc. for C30H33N3: C, 82.72; H, 7.64; N, 9.65. Found: C, 82.89; H, 7.73; N, 9.54. 1H NMR (CDCl3): 8.40-8.42 (m, 2H, CH═N and 3-H in Py), 7.99 (m, 1H, 4-H in Py), 7.91 (d, J=8.4 Hz, 1H, 4-H in naphthyl), 7.87 (m, 1H, 8-H in naphthyl), 7.66 (d, J=8.4 Hz, 1H, 3-H in naphthyl), 7.55 (m, 1H, 5-H in Py), 7.36-7.47 (m, 3H, 5,6,7-H in naphthyl), 6.90 (s, 2H, 3,5-H in mesityl), 3.60 (d, J=10.9 Hz, 1H, CHH′N), 3.53 (d, J=10.9 Hz, CHH′N), 3.40 (s, 1H, NH), 2.29 (s, 3H, 4-Me in mesityl), 2.17 (s, 6H, 2,6-Me in mesityl), 0.96 (s, 9H, tBu).

Provenance & Evidence